Synthesis of (E)-α-ethynyl-α,β-unsaturated esters from allenyl acetates catalyzed by DABCO and their application to sonogashira cross-coupling reactions

Bulletin of the Korean Chemical Society

Volumn 31, Issue 3, 2010, Pages 742-745

  Kim, Hyunseok ^a   Shin, Doosup ^a   Lee, Kwangmoo ^a   Lee, Sangkyu ^a   Kim, Sanghyuk ^a   Lee, Phil Ho ^a  

^a Kangwon National University   (South Korea)

Author keywords

(E) ethynyl unsaturated ester; Allenyl acetate; Catalysis; DABCO; Enyne

Indexed keywords

EID: 77951875475     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.03.742     Document Type: Article

References (49)

1. (a) Tsuboi, S.; Kuroda, H.; Takatsuka, S.; Fukawa, T.; Sakai, T.; Utaka, M. J. Org. Chem. 1986, 58, 5952.
2. (b) Rossi, R.; Bellina, F.; Bechini, C; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135.
3. (c) Shi, W.; Xiao, F.; Wang, J. J. Org. Chem. 2005, 70, 4318.
4. (d) Wang, Y.; Burton, D. J. Org. Lett. 2006, 8, 5295.
5. (e)Pemay, A. B.; Vulic, K. S.; Ogilvie, W. W. J. Org. Chem. 2006, 77, 3615.
6. (f) Psukada, N.; Niomiya, S.; Ayoama, Y.; Inoue, Y. Org. Lett. 2007, 9, 2919.
7. (a)Rossi, R.; Bellina, F.; Bechini, C; Mannina, P.; Vergamini. P. Tetrahedron 1998, 54, 135.
8. (b)Prost, B. M.; Gunzner, J. P.; Yasukata, P. Tetrahedron Lett. 2001, 42, 3775.
9. (c) Dai, W.-M.; Wu, A.; Hamaguchi, W. Tetrahedron Lett. 2001, 42, 4211.
10. (d) Pemay, A.; Vulic, K.; Ogilivie, W. J. Org. Chem. 2006, 77, 3615.
11. Barma, D. K.; Kundu, A.; Zhang, PF; Mioskowski, C; Falck, J. R. J. Am. Chem. Soc. 2003, 725, 3218.
12. (a) Forti, P.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron Lett. 1995, 36, 3023.
13. (b) Kim, K. M.; Park, I. H. Synthesis 2004, 2641.
14. Kruper, W. J., Jr.; Emmons, A. H. J. Org. Chem. 1991, 56, 3323.
15. Alarm, M.; Crousse, B.; Pinstrumelle, G. Tetrahedron Lett. 1995, 36, 3687.
16. Buschmann, E.; Schafer, B. Tetrahedron 1994, 50, 2433.
17. (a) Satoh, P.; Itoh, N.; Onda, K.; Kitoh, Y; Yamakawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 2800.
18. (b) Ishihara, P.; Shintani, A.; Yamanaka, H. Tetrahedron Lett. 1998, 39, 4865.
19. (a) Villieras, J.; Perriot, P.; Normant, J. F. Synthesis 1978, 7, 31.
20. (b)Chan, P.H.;Moreland, M. Tetrahedron Lett. 1978, 6, 515.
21. (c) Karrenbrock, F.; Schaefer, H. J. Tetrahedron Lett. 1979, 57, 2913.
22. (d) Zapata, A.; Ferrer, G. F. Synth. Commun. 1986, 116, 1611.
23. (e) Huang, Z.-Z.; Wu, P.-P.; Zhu, P.-S.; Huang, X. Synth. Commun. 1996, 26, 677.
24. (f) Braun, N. A.; Buerkle, U.; Feth, M. P.; Klein, I.; Spitzner, D. Eur. J. Org. Chem. 1998, 8, 1569.
25. (g) Sano, S.; Ando, T.; Yokoyama, K.; Nagao, Y. Synlett 1998, 777.
26. (h) Tago, K.; Kogen, H. Tetrahedron Lett. 2000, 56, 8825.
27. (a)Denney, D. B.; Ross, S. T. J. Org. Chem. 1962, 27, 998.
28. (b) Yasui, S.; Nakamura, K.; Fujii, M.; Ohno, A. J. Org. Chem. 1985, 50, 3283.
29. (c) Bellina, F.; Carpita, A.; De Santis, M.; Rossi, R. Tetrahedron Lett. 1994, 35, 6913.
30. (d)Rousseau, G.; Marie, J.-X. Synth. Commun. 1999, 29, 3705.
31. (e) Zhang, X.; Qing, F.-L.; Yang, Y.; Yu, J.; Fu, X.-K. Tetrahedron Lett. 2000, 41, 2953.
32. (f) Tago, K.; Kogen, H. Org. Lett. 2000, 2, 1975.
33. (g)Zhang, X.; Qing, F.-L.; Yu, Y. J. Org. Chem. 2000, 65, 7075.
34. (h) Hamelin, J.; Saoudi, A.; Benhaoua, H. Synthesis2003, 2185.
35. (i) Chang, M. Y.; Sun, P. P.; Chen, S. T.; Chang, N. C. Tetrahedron Lett. 2003, 44, 5271.
36. (j) Olpp, T.; Bruckner, R. Synthesis 2004, 2135.
37. (k) Sakamoto, R.; Murata, M.; Nishihara, H. Angew. Chem. Int. Ed. 2006, 45, 4793.
38. (a)Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem. Int. Ed. 2002, 41, 3901.
39. (b)Lee, P. PL; Lee, K. Angew. Chem. Int. Ed. 2005, 44, 3253.
40. (c) Lee, P. PL; Lee, K.; Kang, Y. J. Am. Chem. Soc. 2006, 128, 1139.
41. (d) Kim, PL; Livinghouse, T.; Seomoon, D.; Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 1127.
42. (e)Kim, S.; Lee, K.; Seomoon, D.; Lee, P. U.Adv. Synth. Catal. 2007, 349, 2449.
43. (f) Yu, PL; Lee, P. H.J. Org. Chem. 2008, 73, 5183.
44. (g) Lee, K.; Lee, P. H. Org. Lett. 2008, 10, 2441.
45. (h)Kim, S.; Lee, P. H. Eur. J. Org. Chem. 2008, 2262.
46. (i)Kim, S.; Lee, P. H. Adv. Synth. Catal. 2008, 350, 547.
47. (j) Lee, K.; Lee, P. H. Bull. Korean Chem. Soc. 2008, 29, 487.
48. (k) Park, C; Lee, P. H. Org. Lett. 2008, 10, 3359.
49. (l) Choi, Y.; Lee, P. H. Org. Lett. 2009, 11, 1445.